Record Information
Version1.0
Creation date2010-04-08 22:11:22 UTC
Update date2019-11-26 03:10:27 UTC
Primary IDFDB014612
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrocapsenone
DescriptionDihydrocapsenone is a member of the class of compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Dihydrocapsenone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Dihydrocapsenone can be found in a number of food items such as italian sweet red pepper, red bell pepper, orange bell pepper, and pepper (c. annuum), which makes dihydrocapsenone a potential biomarker for the consumption of these food products.
CAS Number109986-01-8
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.39ALOGPS
logP2.85ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)14.76ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.71 m³·mol⁻¹ChemAxon
Polarizability27.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H24O2
IUPAC name3-hydroxy-4,4a-dimethyl-6-(prop-1-en-2-yl)-decahydronaphthalen-1-one
InChI IdentifierInChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h10-13,16H,1,5-8H2,2-4H3
InChI KeySNEXDCBPEIQRSH-UHFFFAOYSA-N
Isomeric SMILESCC1C(O)CC(=O)C2CCC(CC12C)C(C)=C
Average Molecular Weight236.3499
Monoisotopic Molecular Weight236.177630012
Classification
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0190000000-28ffa9be11f08869a50e2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0170-3970000000-b11f4051da2f7ce8fc182016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9500000000-b1d388c3c115ca0d2f652016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9b23ae9f04e0595b24ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-46094392f8a4c89d58dd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-1960000000-f4f76992501c517655fb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-0960000000-fb69302ae279995cba532021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n0-1930000000-10a9d1916236c2eace682021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9410000000-02c99d550aa8d9f2fbcd2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c0031dc201eac6b6350a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-6aba8a22c99fdb39b61b2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015i-0950000000-66e11945a2245daee5902021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID123389
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJWH26-L:JSX27-M
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00016978
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Green bell pepperExpected but not quantifiedNot AvailableKNAPSACK
Italian sweet red pepperExpected but not quantifiedNot AvailableKNAPSACK
Orange bell pepperExpected but not quantifiedNot AvailableKNAPSACK
PepperExpected but not quantifiedNot AvailableKNAPSACK
Red bell pepperExpected but not quantifiedNot AvailableKNAPSACK
Yellow bell pepperExpected but not quantifiedNot AvailableKNAPSACK
Showing 1 to 6 of 6 entries
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.